Sodium hydride → 5-(3,5-dimethylphenylthio)-4-isopropyl-1H-imidazole

HRID 1415984Notes

Reaction equation

[CH:1]([C:4]1[N:5]=[CH:6][NH:7][C:8]=1I)([CH3:3])[CH3:2].[CH3:10][C:11]1[CH:12]=[C:13]([SH:18])[CH:14]=[C:15]([CH3:17])[CH:16]=1.[H-].[Na+]>CN(C)C=O>[CH3:10][C:11]1[CH:12]=[C:13]([S:18][C:8]2[NH:7][CH:6]=[N:5][C:4]=2[CH:1]([CH3:3])[CH3:2])[CH:14]=[C:15]([CH3:17])[CH:16]=1

Participants

Conditions

Temperature: 140 °C

Procedure

In 30 ml of dry N,N-dimethylformamide was dissolved 4.0 g (16.9. mmol)of 4-isopropyl-5-iodo-1H-imidazole (4b), followed by addition of 4.68 g (33.9 mmol)of 3,5-dimethylthiophenol and 2.1 g (52.5 mmol)of 60% sodium hydride. The mixture was heated at 140° C. for 7 hours. The N,N-dimethylformamide was then distilled off under reduced pressure and, after addition of dry ice, the residue was extracted with methylene chloride. The organic layer was washed with water and dried over sodium sulfate. The solvent was then distilled off under reduced pressure and the residue was fractionated by silica gel chromatography (3% methanol-methylene chloride). The eluted crude compound was recrystallized from ethyl acetate-diisopropyl ether to provide 2.2 g (yield 53%)of 5-(3,5-dimethylphenylthio)-4-isopropyl-1H-imidazole (X=Y=Me) (9).

Workup

distillationThe N,N-dimethylformamide was then distilled off under reduced pressure
additionafter addition of dry ice
extractionthe residue was extracted with methylene chloride
washThe organic layer was washed with water
dry with materialdried over sodium sulfate
distillationThe solvent was then distilled off under reduced pressure
washThe eluted crude compound
customwas recrystallized from ethyl acetate-diisopropyl ether

Sources & evidence

ORD record: ord-d8c2edc9f1c149878fddd0e5fe01d81d
Source dataset: uspto-grants-1999_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05910506

Reaction notes

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